Diisobutylaluminumhydride → HCID 21023777, compound

HRID 1795170Notes

Reaction equation

HRID 1795170 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH2:14][C:15](=[C:18]=[O:19])OC)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)([CH2:14][CH2:15][CH:18]=[O:19])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86590568HCID 86590568, compound

Product 1

HCID 21023777HCID 21023777, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−78° C.) solution of 4-cyclohexyl-4-(2-methoxy-carbonylethyl)-piperidine-1-carboxylic acid tert-butyl ester, 9, (1.0 g, 2.833 mmol) in 40 ml of anhydrous methylene chloride is added diisobutylaluminum hydride (5.75 ml, 1 M, 5.75 mmol). The reaction is stirred at room temperature for 40 min before it is quenched by adding methanol (3 mL) and water (20 mL). The reaction mixture is warmed to room temperature and the organic layer separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford 915 mg (>99% yield) of the desired compound as a colorless oil.

Workup

  1. customis quenched
  2. additionby adding methanol (3 mL) and water (20 mL)
  3. temperatureThe reaction mixture is warmed to room temperature
  4. customthe organic layer separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d594b9b91b6a4183a02728c06c55ebfa
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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